


Next Year: Part 2

by wingedcatninja



Series: SPN Kink Bingo 2020 [2]
Category: Supernatural
Genre: Bondage, Bottom Dean Winchester, F/M, Femdom, Pegging, SPN Dean Bingo 2019, St. Andrew's Cross, Sub Dean, Sub!Dean, Submissive Dean Winchester, Woman on Top, first time pegging
Language: English
Status: Completed
Published: 2020-01-27
Updated: 2020-01-27
Packaged: 2021-02-27 03:54:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 972
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22440664
Author URL: https://archiveofourown.org/users/wingedcatninja/pseuds/wingedcatninja
Summary: After the impact play, Dean gets pegged.
Relationships: Dean Winchester/Original Female Character(s), Dean Winchester/You
Series: SPN Kink Bingo 2020 [2]
Series URL: https://archiveofourown.org/series/1612531
Comments: 8
Kudos: 27
Collections: SPN Kink Bingo 2020





	Next Year: Part 2

**Author's Note:**

> Continuation of [Dean’s visit to Vegas](https://archiveofourown.org/works/22407037). I apologize for nothing.
> 
> Square Filled (@spnkinkbingo): Pegging

His eyes on her, she moved over to the table, reaching into another box, similar to the one that held the plugs. His mind was too relaxed to wonder at the bundle of leather straps she pulled out. Staying in his field of vision, she pulled the dress over her head and draped it over a chair back before stepping into the harness. Deft fingers quickly adjusted the straps, buckling the buckles and tucking the loose ends under where they would be out of the way. 

She reached into the box again, rummaging for a moment before producing a rather slim dildo of purple silicone. She held it up for him to see, her fingers caressing it lovingly.

“This’ll do nicely. What do you think, Dean? Can you imagine me fucking you with this? Feeling it slide into your ass?” She enjoyed teasing him, and judging by the way his cock twitched at her words, so did he.

She fitted the dildo into the harness and made sure Dean watched while she coated the dildo with lube until it glistened, her hand easily sliding along the length of it. She wiped her hands on a towel, then moved in close to Dean again, keeping her eyes on his. Her fingers tangled in his hair, gripping a handful of the sweat-damp strands. 

“Will this be your first time, Dean? Getting fucked, I mean?” She kept her tone even, not wanting to jolt him out of his headspace while she checked in.

He managed to nod, in spite of her grip on his hair. 

“You remember your safeword?” She asked him, still in the same even tone.

Dean nodded again, but she needed to hear him say it. It took him a moment to find his voice.

“Apples,” he managed finally, the word coming out in a hoarse whisper.

“Good boy,” she praised him. “I’m gonna enjoy fucking you, Dean. I’m gonna make you feel so good.”

She kissed him, her tongue licking into his mouth to taste him fully. She swallowed the soft moan he let out, feeling it like a shiver through her body. When she let him go, they were both breathing hard, his eyes just slightly unfocused.

Returning to her position behind him, she moved in until her breasts were pressed against his back. His welted skin was hot against hers. She slid one arm around him, splaying her fingers over his chest, her lips pressing tender kisses between his shoulder blades. 

Deft fingers found the base of the plug that was still in his ass. Slowly, teasingly, she pulled it out half-inch by half-inch, until it was free. She dropped it on the floor, fingers already wrapped around the base of her silicon cock, holding it steady. 

Dean’s breath hitched when he felt the tip press against his hole. Focusing on his breathing, and her body pressed against his, he forced himself to relax into her touch. She felt it when he did, and that was when she moved her hips, pressing the dildo slowly against his muscle. 

Her breath fanned over his back with her whispered words of assurance. The strap-on inched inside him inexorably until her hips were pressed against his ass. She wrapped the other arm around him as well, hugging him from behind, peppering kisses across his back. She rolled her hips, the dildo moving inside him, rubbing against his prostate. Dean huffed out a sigh of pleasure at the feeling. 

It took her a moment to find the right angle, but once she did, she set a slow, sensuous pace, each thrust hitting just right inside him to send sparks of pleasure through his body. With her pressed against him so closely, he felt each welt on his back intensely, but instead of detracting from the pleasure, the sting added to it. 

Her fingers wrapped around his cock, stroking slowly in time with her thrusts. A low moan came from deep in his chest at the intense stimulation. He wanted to move, to thrust back against her, to wrap his arms around her, kiss her; the fact that he was unable to, helpless in her power, only added to his pleasure. 

Her other hand ventured lower, cradling his balls, squeezing gently. Dean groaned, her name falling from his lips like a prayer. Another time, another place, he might have been embarrassed at how quickly he found himself on the edge of bliss, but right then and there it seemed like a ridiculous thing to worry about.

Her voice coaxed him on, encouraged him to let go, so he did. Hands gripping the beams of the cross, he shook in her embrace, white drops falling onto the dark-painted floor beneath him. For those few moments, everything fell away, all the shitty things that had been going on lately, and he floated, weightless, without a care. 

He felt her pull out and move away from him as if he was outside himself, disconnected. Her slow and tender kiss pulled him back into his body.  Her hands stroked his skin soothingly, watching him closely. She saw his eyes come back into focus and smiled softly at him. 

* * *

The next morning, after Dean had pulled on his boots, she wrapped her arms around him in a tender hug. He hugged her back, holding her like he never wanted to let go. When she loosened her grip though, he did, allowing her to take half a step back so she could look him in the eyes. She could tell there was still a lot of darkness in him, but it seemed to weigh on him less than the night before.

Dean squeezed her hand gently and smiled, perhaps a smidge wistfully.

“I’ll see you next year.”

And then he was gone, back to the life she knew nothing about.


End file.
